Oakland Vacations from $178
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Price was $243, price is now $178 per person
$178
per person
Jan 8 - Jan 10
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8/10 Very Good! (1,014 reviews)
Everything went smooth and a great value. Neighborhood is lacking options and few minor inconveniences kept it from 5 stars (for the price).
Reviewed on Oct 29, 2025
Hilton Garden Inn Pittsburgh Airport
Price was $656, price is now $482 per person
$482
per person
Dec 1 - Dec 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,009 reviews)
My stay was great the only thing that was not so great was housekeeping came to clean our room 1 time out of 3 nights and didn’t even clean our room they forgot there cleaning spray bottle in the restroom. But nothing was done.
Reviewed on Oct 29, 2025
Fairmont Pittsburgh
Downtown Pittsburgh
Price was $800, price is now $608 per person
$608
per person
Jan 8 - Jan 10
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.8/10 Excellent! (1,008 reviews)
Everything was wonderful! I will be back next yer for sure
Reviewed on Oct 29, 2025
DoubleTree by Hilton Pittsburgh - Green Tree
Price was $475, price is now $363 per person
$363
per person
Dec 1 - Dec 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,029 reviews)
Room was clean and entire hotel appeared very clean . Staff was very friendly and pleasant
Reviewed on Oct 29, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $136 total per night from Nov 3 to Nov 4
$136 total
Nov 3 - Nov 4
Total with taxes and fees
8.8/10 Excellent! (482 reviews)
Rom was good but my 2 sons and I had breakfast that had cold toast and just warm sausage and eggs. My sons that had burritos were presented ok
Reviewed on Oct 27, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive, Pittsburgh, PA
Fully refundable
$111 nightly
The price is $127 total per night from Nov 23 to Nov 24
$127 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Clean nicely decorated, and the shuttle service was a plus
Reviewed on Oct 16, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Nov 23 to Nov 24
$214 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (698 reviews)
Clean room. Friendly staff. Great room service. Able to honor disability accommodation. Very helpful.
Reviewed on Oct 20, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Ghosts Steel City Haunted Tour
$26
per adult
100% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
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- Clemente Museum
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- Contemporary Craft
- Market Square
- Visit Pittsburgh
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- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.